Manufacture of sulphocyano derivatives



' by weight: 4 a

1.13.5 parts of sulphuryl- Patented Aug. 3, 1926.

UNITED STATES PATENT OFFICE.

OSKAR SPENGLEB, OF I DESSAU ANHEIM, AND WERNER Mtl'LLEB, OF LEIPZIG, GER- MANY, ASSIGNORS TO ACTIEN BERLIN, GERMANY.

GESELLSCHAFT FUR ANILIN FABRIKATION, OF

MANUFACTURE, OF SULPHOCYAN'O DERIVATIVES.

No Drawing. Application filed September 2,

Free thiocyanogen has been prepared by the action of iodine, bromine or chlorine upon the sulphocyanide of lead, mercury or silver. with the exception that the action 5 of chlorine on lead'has not so far proved to be a method of obtaining the free thiocyanogen.

According to the present action in a suitable solvent of sulphuric acid and a sulphocyanide, for example lead sulphocyanide, produces a solution which contains a compound which easily decomposes into thiocyanogen and sulphurous acid. One can assume the produc- 5 tion of a sulphuryl sulphocyanide as an intermediate stage in the reaction between a sulphocyanide and sulphuryl chloride for example. Solutions produced in this manner are suitable. for introducing the sulphocyanogen residue into organic compounds, by causing the solution to reactwith them for instance with. an hydroxaryl compound. The following examples illustrate the invention without limiting it, the parts being Ewample chloride are dissolved in 400 parts of carbontetrachloride and an excess of finely powdered leadsulphocyanide is introduced.

A lively reac -ion sets in at once and'after some time the reaction is completed. The leadchloride and excess of sulphocyanide are separated by filtration and the 'filtrate is mixed with a cold solution of 14.5 parts of 1- hydroxynaphthalenein carbontetrachloride.

invention, the re-. between a halide 1925, Serial No. 54,131, and in Germany September 24,1924.

A lively evolution of hydrogensulphocyanide ensues while the liquid becomes turbid and there separates gradually from it a brownish crystalline mass which after 7 further purification proves to be 4-sulphocyano-1- hydroxynaphthalene of melting point 111- 112 C. A sample of it mixed with a com-- pound obtained by Deutschen Pharmazeutischen Gesellschaft 33, page 144) did not show a lower melting point. 3

-It is obvious to those skilled in the art that our present invention is not limited to the foregoing example or to the details given therein. It may be stated, for instance, that instead of the l-hydroxynaphthalene employed in the foregoing example any hydroxyaryl compound may be used. It is obvious that in. employing such other hydroxyaryl compound the proportions of the ingredients as well as the other special conditions of reaction may be altered in order to obtain the .best results.

What we claim is,-- The hereindescribed manufacture of sulphooyano-derivatives by'causing a solution containing a product of the reaction between a halide of sulphuric acid and a $111- phocya'nide to react with aromatic hydrox- H yaryl compounds.

'In testimony whereof we afiix our signatures.

OSKAR sPiiuoLER.

WERNER MULLER.

Kaufmann (Berichte der 

